Pyrimidine sulfamate fungicides

Abstract

Pyrimidine derivatives are provided wherein the 6-position carries the group OSO2NR5R6 and the 2-position carries the group NR1R2. R1 and R2 are preferably hydrogen or lower alkyl but both are not hydrogen and R5 and R6 are preferably lower alkyl, although these groups may form a cyclic ring. The 3-position and 4-position are preferably substituted with lower alkyl, although lower alkynyl or alkenyl may be used. The derivatives are compounded into compositions for combatting fungal pests.

We claim: 
     
       1. A fungicidal composition comprising, as an active ingredient, a fungicidally effective mount of a pyrimidine sulphamate derivative having the formula: ##STR35## or a salt thereof, wherein R 1  and R 2  are hydrogen or lower alkyl, lower alkynyl or lower alkenyl but are not both hydrogen, or together with the adjacent N-atom form a monocyclic 5-, 6- or 7-ring atom heterocyclic group, optionally interrupted by an additional hetero atom selected from the group consisting of O, N and S; R 3  and R 4  are lower alkyl, lower alkynyl or lower alkenyl; and R 5  and R 6  are lower alkyl, lower alkynyl or lower alkenyl or together with the adjacent N-atom form a monocyclic 5-, 6- or 7-ring atom heterocyclic group, optionally interrupted by an additional hetero atom selected from the group consisting of O, N and S, and a carrier for the active ingredient. 
     
     
       2. A composition according to claim 1 wherein the sulphamate derivative has the formula: ##STR36## or a salt thereof, wherein R 1  and R 2  are hydrogen, methyl, ethyl, or allyl, but are not both hydrogen; and R 5  and R 6  are methyl, ethyl, propyl or butyl or together with the adjacent N-atom form a pyrrolidino, morpholino, piperidino, piperazino or azepino ring, optionally substituted with methyl. 
     
     
       3. A composition according to claim 1 wherein the alkyl and alkenyl groups contain from 1 to 4 carbon atoms, and from 3 to 4 carbon atoms, respectively. 
     
     
       4. A composition according to claim 1 wherein the alkyl groups are methyl, ethyl, propyl or butyl and the alkenyl groups are allyl or butenyl. 
     
     
       5. A composition according to claim 1 wherein the heterocyclic groups are selected from pyrrolidino, morpholino, piperidino, piperazine or azepino rings. 
     
     
       6. A composition according to claim 1 wherein R 1 , R 2  and R 3  are methyl, R 4  is n-butyl and R 5  and R 6  form piperidino. 
     
     
       7. A composition according to claim 1 wherein R 1 , R 2  and R 3  are methyl, R 4  is n-butyl and R 5  and R 6  form pyrrolydino. 
     
     
       8. A composition according to claim 1 wherein R 1 , R 2  and R 3  are methyl, R 4  is n-butyl and R 5  and R 6  form morpholino. 
     
     
       9. A composition according to claim 1 wherein R 1  is hydrogen, R 2  is ethyl, R 3  is methyl, R 4  is n-butyl and R 5  and R 6  form pyrrolidino. 
     
     
       10. A composition according to claim 1 wherein R 1  is hydrogen, R 2  is ethyl, R 3  is methyl, R 4  is n-butyl and R 5  and R 6  are both ethyl. 
     
     
       11. A composition according to claim 1 wherein R 1  is hydrogen, R 2  is n-propyl, R 3  is methyl, R 4  is n-butyl and R 5  and R 6  form pyrrolidino. 
     
     
       12. A composition according to claim 1 wherein R 1  is hydrogen, R 2  is iso-propyl, R 3  is methyl, R 4  is n-butyl and R 5  and R 6  form pyrrolidino. 
     
     
       13. A composition according to claim 1 wherein R 1  and R 2  are hydrogen or lower alkyl, and R 3 , R 4 , R 5  and R 6  are lower alkyl. 
     
     
       14. A process for combatting fungi which comprises treating plants or seeds with a composition comprising, as an active ingredient, an effective amount of a pyrimidine sulphamate derivative having the formula: ##STR37## or a salt thereof, wherein R 1  and R 2  are hydrogen or lower alkyl, lower alkynyl or lower alkenyl but are not both hydrogen, or together with the adjacent N-atom form a monocyclic 5-, 6- or 7-ring atom heterocyclic group, optionally interrupted by an additional hetero atom selected from the group consisting of O, N and S; R 3  and R 4  are lower alkyl, lower alkynyl or lower alkenyl; and R 5  and R 6  are lower alkyl, lower alkynyl or lower alkenyl or together with the adjacent N-atom form a monocyclic 5-, 6- or 7-ring atom heterocyclic group, optionally interrupted by an additional hetero atom selected from the group consisting of O, N and S. 
     
     
       15. A process according to claim 14 wherein the sulphamate derivative has the formula: ##STR38## or a salt thereof, wherein R 1  and R 2  are hydrogen, methyl, ethyl, or allyl, but are not both hydrogen; and R 5  and R 6  are methyl, ethyl, propyl or butyl or together with the adjacent N-atom form a pyrrolidino, morpholino, piperidino, piperazine or azepino ring, optionally substituted with methyl. 
     
     
       16. A process according to claim 14 wherein the alkyl and alkenyl groups contain from 1 to 4 carbon atoms, and from 3 to 4 carbon atoms, respectively. 
     
     
       17. A process according to claim 16 wherein the alkyl groups are methyl, ethyl, propyl or butyl and the alkenyl groups are allyl or butenyl. 
     
     
       18. A process according to claim 14 wherein the heterocyclic groups are selected from pyrrolidino, morpholino, piperidino, piperazine or azepino rings. 
     
     
       19. A process according to claim 14 wherein R 1 , R 2  and R 3  are methyl, R 4  is n-butyl and R 5  and R 6  form piperidino. 
     
     
       20. A process according to claim 14 wherein R 1 , R 2  and R 3  are methyl, R 4  is n-butyl and R 5  and R 6  form pyrrolidino. 
     
     
       21. A process according to claim 14 wherein R 1 , R 2  and R 3  are methyl, R 4  is n-butyl and R 5  and R 6  form morpholino. 
     
     
       22. A process according to claim 14 wherein R 1  is hydrogen, R 2  is ethyl, R 3  is methyl, R 4  is n-butyl and R 5  and R 6  form pyrrolidino. 
     
     
       23. A process according to claim 14 wherein R 1  is hydrogen, R 2  is ethyl, R 3  is methyl, R 4  is n-butyl and R 5  and R 6  are both ethyl. 
     
     
       24. A process according to claim 14 wherein R 1  is hydrogen, R 2  is n-propyl, R 3  is methyl, R 4  is n-butyl and R 5  and R 6  form pyrrolidino. 
     
     
       25. A process according to claim 14 wherein R 1  is hydrogen, R 2  is iso-propyl, R 3  is methyl, R 4  is n-butyl and R 5  and R 6  form pyrrolidino. 
     
     
       26. A process according to claim 14 wherein R 1  and R 2  are hydrogen or lower alkyl, and R 3 , R 4 , R 5  and R 6  are lower alkyl.